130983-15-2

Upstream product

• 54976-38-4 (E)-3-phenylbut-2-en-1-ol 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 98-86-2 acetophenone 

Downstream Products

• 116183-49-4 (2R,3S)-3-phenyl-butane-1,2-diol 
• 130942-58-4 1-hydroxy-3-methyl-3-phenylpropan-2-one 
• 365442-07-5 (2R,3R)-3-tert-butoxycarbonylamino-3-phenylbutan-1,2-diol 
• 365442-14-4 (R)-2-((tert-butoxycarbonyl)amino)-2-phenylpropanoic acid 

Relevant academic research and scientific papers

C-O hydrogenolysis catalyzed by Pd-PMHS nanoparticles in the company of chloroarenes

Catalytic Pd(OAc)2 and polymethylhydrosiloxane (PMHS), in conjunction with aqueous KF, and a catalytic amount of an aromatic chloride, effects the chemo-, regio-, and stereoselective deoxygenation of benzylic oxygenated substrates at room temperature in THF. Preliminary mechanistic experiments suggest the process to involve palladium-nanoparticle-catalyzed hydrosilylation followed by C-O reduction. The chloroarene additive appears to facilitate the hydrogenolysis process through the slow controlled release of HCl.

Prompt determination of absolute configuration for epoxy alcohols via exciton chirality protocol

A microscale protocol for determination of absolute configurations of 2,3-epoxy alcohols is described. 2,3-Disubstituted (cis and trans), 2,2-disubstituted, 2,2,3-trisubstituted, and 2,3,3-trisubstituted epoxy alcohols rendered prominent ECCD signals upon complexing with a Lewis acidic porphyrin tweezer and consequently provide straightforward assignment of chirality for epoxy alcohols. This method proved to be rapid, simple, sensitive, and reliable for the class of molecules listed above. Copyright

Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model

(Chemical Equation Presented) Bishydroxamic acid derivatives are used as ligands for a vanadium catalyst in the preparation of epoxy alcohols (see scheme). The methodology uses aqueous tert-butyl hydroperoxide (TBHP) as an achiral oxidant, low catalyst loading, low reaction temperatures (0°C to room temperature), and simple workup procedures. The reaction is applied to the kinetic resolution of a secondary allylic alcohol and the preparation of small epoxy alcohols. R1, R2, R3: alkyl, aryl, H.

Catalytic asymmetric epoxidation

The present invention relates to the synthesis of chiral epoxides via a catalytic asymmetric oxidation of olefins. Additionally, the methodology provides a method of asymmetrically oxidizing sulfides and phosphines. This asymmetric oxidation employs a catalyst system composed of a metal and a chiral bishydroxamic acid ligand, which, in the presence of a stoichiometric oxidation reagent, serves to asymmetrically oxidize a variety of substrates.

A new method for the enantioselective synthesis of N-Boc-α,α-disubstituted α-amino acids

A new method for the enantioselective synthesis of N-Boc-α,α-disubstituted α-amino acids has been developed. The starting materials are diastereomerically pure 3,3-disubstituted allyl alcohols, prepared by DIBAL-H reduction of the corresponding unsaturate

Design of optically active hydroxamic acids as ligands in vanadium- catalyzed asymmetric epoxidation

New optically active hydroxamic acids bearing a 1,1'-binaphthyl group were prepared as ligands in a vanadium-catalyzed asymmetric epoxidation. The feature of these hydroxamic acids is a sterically hindered ligand. The asymmetric epoxidation with good selectivity and reactivity can be established by using VO(O-i-Pr)3 (5 mol%) and a small excess amount of ligand (7.5 mol%) with triphenylmethyl hydroperoxide (TrOOH) in toluene at - 20 °C. Disubstituted allyl alcohols were epoxidized more rapidly than mono- or tri-substituted allyl alcohols, and were obtained in good to high enantioselectivities (48 - 94%ee). The transition state based on X-ray crystal structure of 1e is discussed.

ENANTIOSELECTIVE SYNTHESES OF 2-ARYLPROPANOIC ACIDS: (S)-2-PHENYLPROPANOIC ACID

(S)-2-Phenylpropanoic acid, an intermediate for the preparation of optically active Ibuprofen, has been synthesized using, as the key steps, Sharpless epoxidation and benzylic hydrogenolysis.